Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers

Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbe...

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Veröffentlicht in:Journal of organic chemistry 2024-06, Vol.89 (11), p.7630-7643
Hauptverfasser: Liu, Yuheng, Yuan, Lutong, Dai, Linlong, Zhu, Qiaohong, Zhong, Guofu, Zeng, Xiaofei
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container_end_page 7643
container_issue 11
container_start_page 7630
container_title Journal of organic chemistry
container_volume 89
creator Liu, Yuheng
Yuan, Lutong
Dai, Linlong
Zhu, Qiaohong
Zhong, Guofu
Zeng, Xiaofei
description Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. NHC desymmetrization produces axially chiral diaryl ether atropisomers with high yields and enantioselectivities in moderate circumstances. Chiral diaryl ether compounds may be precursors for highly functionalized diaryl ethers with bioactivity and chiral ligands for asymmetric catalysis.
doi_str_mv 10.1021/acs.joc.4c00330
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Org. Chem</addtitle><date>2024-06-07</date><risdate>2024</risdate><volume>89</volume><issue>11</issue><spage>7630</spage><epage>7643</epage><pages>7630-7643</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. NHC desymmetrization produces axially chiral diaryl ether atropisomers with high yields and enantioselectivities in moderate circumstances. 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subjects bioactive properties
carbenes
catalytic activity
chemotypes
esterification
heterocyclic nitrogen compounds
ligands
organic chemistry
stereoselective synthesis
title Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers
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